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[ CAS No. 53631-18-8 ] {[proInfo.proName]}

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Chemical Structure| 53631-18-8
Chemical Structure| 53631-18-8
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Product Details of [ 53631-18-8 ]

CAS No. :53631-18-8 MDL No. :MFCD00109756
Formula : C8H6BrFO Boiling Point : -
Linear Structure Formula :- InChI Key :ITAQNNGDCNFGID-UHFFFAOYSA-N
M.W : 217.04 Pubchem ID :2737451
Synonyms :

Calculated chemistry of [ 53631-18-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.46
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.185 mg/ml ; 0.000851 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.589 mg/ml ; 0.00272 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.89
Solubility : 0.028 mg/ml ; 0.000129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 53631-18-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53631-18-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 53631-18-8 ]
  • Downstream synthetic route of [ 53631-18-8 ]

[ 53631-18-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 455-36-7 ]
  • [ 53631-18-8 ]
YieldReaction ConditionsOperation in experiment
83% With Oxone; ammonium bromide In methanol for 2 h; Reflux General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.
79% With bromine In chloroform at 20℃; Intermediate 119. 2-bromo-1-(3-fluorophenyl)ethanone; To a solution of 1-(3-fluorophenyl)ethanone (5 g, 36.2 mmol) in chloroform (34 mL) was added dropwise a solution of bromine (1.77 mL, 34.56 mmol) in chloroform (89 mL). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was dissolved in methylene chloride (90 mL) and neutralized with sodium hydrogen carbonate (30 mL). The mixture was stirred for some minutes. The organic layer was extracted and washed with water, brine and dried (MgSO4). The solvent was removed under reduced pressure to give the title compound (5.99 g, 79 percent).
62% With N-Bromosuccinimide In ethyl acetate at 40℃; 10mmol 3-fluoroacetophenone is added to a 100mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS),35mL of ethyl acetate dissolved,Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted. After TLC tracks the reaction,The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, and the filtrate was spin-dried.Column chromatography (eluent: petroleum ether/dichloromethane) gave a pale yellow solid with a yield of 62percent.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582
[3] Patent: WO2008/46598, 2008, A1, . Location in patent: Page/Page column 92
[4] RSC Advances, 2014, vol. 4, # 107, p. 62308 - 62320
[5] Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7312 - 7317
[6] Patent: CN107629022, 2018, A, . Location in patent: Paragraph 0454; 0455; 0456; 0457
[7] Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 123 - 149
[8] Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 7, p. 569 - 573
[9] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1291 - 1295
[10] Patent: EP1357116, 2003, A1, . Location in patent: Page/Page column 9
[11] Patent: EP1043319, 2000, A1,
[12] Patent: US2006/14958, 2006, A1, . Location in patent: Page/Page column 13
[13] Patent: WO2012/27965, 2012, A1, . Location in patent: Page/Page column 27-28
[14] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6764 - 6768
[15] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 692 - 702
[16] Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 259 - 268
[17] Organic Letters, 2014, vol. 16, # 1, p. 302 - 305
[18] Chemical Communications, 2014, vol. 50, # 51, p. 6726 - 6728
[19] MedChemComm, 2015, vol. 6, # 6, p. 1036 - 1042
[20] Chemical Communications, 2016, vol. 52, # 29, p. 5152 - 5155
[21] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 8, p. 1166 - 1173
[22] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674
[23] Organic and Biomolecular Chemistry, 2016, vol. 14, # 34, p. 8026 - 8029
[24] Patent: CN105669586, 2016, A, . Location in patent: Paragraph 0066
[25] Journal of Medicinal Chemistry, 2017, vol. 60, # 4, p. 1591 - 1597
[26] Organic Letters, 2017, vol. 19, # 8, p. 1994 - 1997
[27] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 13, p. 3298 - 3314
[28] Organic Letters, 2017, vol. 19, # 11, p. 2877 - 2880
[29] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
  • 2
  • [ 67-56-1 ]
  • [ 455-36-7 ]
  • [ 1353125-19-5 ]
  • [ 53631-18-8 ]
YieldReaction ConditionsOperation in experiment
39% at 20℃; for 24 h; General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
  • 3
  • [ 350-51-6 ]
  • [ 53631-18-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9889 - 9894
[2] Tetrahedron, 2018, vol. 74, # 27, p. 3602 - 3607
  • 4
  • [ 402-63-1 ]
  • [ 53631-18-8 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 10, p. 3710 - 3714
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